David Coleman Headley was a wildly elusive figure who juggled allegiances with militant groups and security agencies in Pakistan while manipulating and betraying wives, friends and allies. A heroin addict turned drug informant turned militant jihadist and Pakistani spy, he played a pivotal role in planning the deadly 2008 Mumbai attacks. U.S. authorities had numerous tips about Headley prior to the attacks, and Indian officials believe he was a double agent working for the U.S. Headley wasn’t arrested until October 2009, when he was plotting a second attack against Denmark.